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Design and Synthesis of Some New 1,3,4-Thiadiazines with Coumarin Moieties and Their Antioxidative and Antifungal Activity

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Department of Applied Chemistry and Ecology, Faculty of Food Technology, J. J. Strossmayer University, Franje Kuhača 20, Osijek 31 000, Croatia
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Department of Biology, J. J. Strossmayer University, Cara Hadrijana 8/A, Osijek 31 000, Croatia
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Author to whom correspondence should be addressed.
Molecules 2014, 19(1), 1163-1177; https://doi.org/10.3390/molecules19011163
Received: 12 December 2013 / Revised: 13 January 2014 / Accepted: 14 January 2014 / Published: 17 January 2014
(This article belongs to the Section Organic Chemistry)
A series of newly disubstituted (compounds 4a,b) and trisubstituted 1,3,4-thiadiazines 5al with various substituents was prepared utilizing different thiosemicarbazides and 3-α-bromoacetylcoumarins as starting compounds. The structures of the synthesized 1,3,4-thiadiazines are elucidated and confirmed utilizing the corresponding analytical and spectroscopic data. All of the new thiadiazine derivatives were tested for their antioxidant activity, employing different antioxidant assays (DPPH scavenging activity, iron chelating activity, power reducing activity). Compounds 5b, 5f, 5j and 4b were proven to be the best DPPH radical scavengers, while compounds 5h and 5j have shown the best iron chelating activity. Thiadiazine derivatives were also tested on their antifungal activity against four mycotoxicogenic fungi, Aspergillus flavus, A. ochraceus, Fusarium graminearum and F. verticillioides. The best antifungal against A. flavus was proven to be compound 5e, while compounds 4a and 5c were the best antifungals on A. ochraceus, and compound 5g showed the best antifungal activity on F. verticillioides. View Full-Text
Keywords: coumarin; 1,3,4-thiadiazines; thiosemicarbazides; antifungal activity; antioxidative activity coumarin; 1,3,4-thiadiazines; thiosemicarbazides; antifungal activity; antioxidative activity
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Čačić, M.; Pavić, V.; Molnar, M.; Šarkanj, B.; Has-Schön, E. Design and Synthesis of Some New 1,3,4-Thiadiazines with Coumarin Moieties and Their Antioxidative and Antifungal Activity. Molecules 2014, 19, 1163-1177.

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